


Trying Something New

by babyjared



Category: Supernatural
Genre: Anal Sex, Bottom!Sam, Fingering, Friends to Lovers, Kissing, M/M, Plot What Plot/Porn Without Plot, Rimming, Smut, Student!Dean, Unrelated Dean Winchester/Sam Winchester, Unrelated Winchesters, student!Sam, top!dean
Language: English
Status: Completed
Published: 2015-07-05
Updated: 2015-07-05
Packaged: 2018-04-07 18:22:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,144
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4273368
Author URL: https://archiveofourown.org/users/babyjared/pseuds/babyjared
Summary: <blockquote class="userstuff">
              <p>Dean's been wondering about his friend, Sam, for a while now. Sam's just broken up with his boyfriend, and Dean takes his chance. Basically just porn, guys</p>
            </blockquote>





	Trying Something New

**Author's Note:**

> This was written as a reader insert on my tumblr (deans-colette) so if there are mistakes, sorry!

Dean had never been so conflicted. He wasn’t one to be attracted to…guys, but something about him, he just couldn’t help himself. He cleared his throat and looked across the table at him, studying how he was so focused on his assignment, “So uh, Sam, you uh…you and Matthew didn’t work out I take it?”

Sam looked up at Dean, trying not to get lost in his eyes, “Yeah, no I guess he’s not really…my type” he said, squirming in his chair a bit. 

Dean bit his lip and Sam’s eyes were instantly drawn to them, “Well then…what is…your type?” he asked cautiously, not really sure how he should go about this. He knew Sam was gay, obviously, but…he was Dean Winchester.

Sam shifted his eyes around the room, “Uh…just…why?”

Dean’s eye brows perked up and he licked his lips, like he always did when he was nervous, “I-I don’t, I just was wondering if you-I-”

The younger boy smirked at his odd nervousness and stood up to sit next to him, seeing how Dean’s eyes followed his every move. Sitting down next to him, he looked into his eyes, “Dean…do you…want something?”

Dean sighed and watched Sam lick his lips, “I-” he cracked an awkward smile, “I’m not really sure”

Sam took a chance and slid his hand across the table, grazing his fingers with Dean’s. He flinched, but didn’t move them, and Sam watched him watch his hand as it moved up his arm, slowly. Dean looked over at the dark haired boy and felt his breath quicken. Sam’s hand got to his bicep, stopped, and he leaned in, “Dean”

“Sam…I-”

“Shh…it’s okay Dean,” he whispered, leaning in closer, inches away from Dean’s lips, Sam looked up to see Dean’s eyes closed, he smiled before leaning closer and finally placing his lips against his. Sam peeked to see Dean’s brows furrowed, and closed his own again, pressing a bit harder. The younger boy did’t move, until he felt him kiss back, moving his lips against Sam’s. Hi hands moved up to cup Dean’s face, pulling him closer, slanting his lips to the blondes, and licking his bottom lip. Dean gasped and opened for Sam, his hand shaking slightly as he brought it to the young boys face. 

Dean had never felt anything like this, but something snapped and he kissed Sam harder, taking control of the kiss. Sam moaned and moved to cup the back of his head, running his hand through Dean’s hair. He moved his other hand to his thigh, sliding it up his muscular leg, hearing Dean’s breath hitch as Sam palmed his crotch. Dean pulled away from the kiss, breathing heavily and looking at Sam, “I’ve never..”

“I know…It’s…almost the same, just…relax”

Dean licked his lips before crashing his lips to Sam’s again, this time, his tongue dominating his as Sam rubbed him through his jeans. Dean groaned and Sam felt him growing harder. The younger boy reached for the button and quickly opened his jeans, slipping his hand inside and finding his thick cock. Dean gasped and moaned, standing up and bringing Sam with him, letting his jeans fall to the ground as Sam pushed him against the table, keeping hold of his cock and pumping it slowly.

Dean moaned and reached down, unbuckling Sam’s pants, pulling his boxers off and grabbing his cock. Sam groaned at the feeling of Dean’s rough hands against him, “Oh god” Sam grunted.

Dean was not entirely sure how he felt about having another man’s cock in his hand, but the sounds Sam was making made it worth the unfamiliar weight. He copied Sam’s movements and felt him harden at his touch. Lifting off his shirt and then Sam’s, the younger boy ran his hands up Dean’s chest, loving the way his muscles twitched. Sam brought him closer, their lips still locked before Sam dropped to his knees and looked up at the older boy. Dean was panting and looking down at Sam as he licked up his cock, he gasped and his hand flew to Sam’s head, “Fuck, S-Sam…I-fuck”

Sam did it again before taking him in fully, loving the feel the feeling of his velvety skin and the feeling of his heavy cock in his mouth as he bobbed his head, listening to  
Dean’s groans as he lightly thrusted into Sam’s mouth. “Oh god….son of bitch, Sam”

His cock hit the back of Sam’s throat, but he took it deeper making the blonde moan loudly, his hand tightening in Sam’s hair, making him moan around Dean’s cock as he fondled his balls, “Holy fuck!” he grunted, thrusting again. 

Sam took a risk and brought his hand around, squeezing Dean’s tight ass before running a finger over his rim. Dean gasped, “D-Do that again” 

Sam deep throated him and used some of the spit dripping down his chin, then running it across his rim again before slipping it inside, “Fuck! God Sam-ah, so good”  
Moaning around him and taking him impossibly deeper, Sam hit his prostate and felt him shudder as he shot down the younger boys throat with a grunt and a hard thrust, “Fucking holy, son of a bitch! Fuck Sam!” 

Sam popped off of him, swallowing everything Dean gave him, and looking up at his panting face. Dean gazed at him before pulling him up and crashing his lips to Sam’s again, groaning as he tasted himself. Sam ran his hands down his body, feeling his muscles tense and then relax under his hands. He pulled away from the kiss, mouthing Sam’s neck before biting at his ear, “I-I want to make you feel good” he grumbled against him, his hand finding Sam’s cock once more.

The younger boy nodded and moaned, watching him drop to his knees. “Oh god” the site of Dean kneeling in front of him, his gaze locked on his erect cock made Sam’s breath hitch, “J-Just do…what you like”

Dean licked his lips before giving Sam’s tip a kitten lick, making him shudder. Dean was not sure if he could actually take Sam in all the way, he had never done this before, but he was determined to make Sam feel as good as he made him feel.

The site of Dean wrapping his full lips around his cock, closing his eyes and bobbing his head, made Sam grunt and moan out his name. Dean moved faster, pressing his tongue to the underside of Sam’s shaft and using his hand to jack off the rest he could’t fit in his mouth, “Oh fuck, Dean, that’s it…Ahh yeah, just like that”

Dean moaned around Sam, letting his big hands squeeze his ass and push him further into his mouth, chocking a little, but he wanted more. Sam grabbed one of his hands and sucked a finger into his mouth, making him grunt. Sam licked it until it was soaked, bringing it back down to his ass, “Please Dean”

He closed his eyes and took a deep breath through his nose before opening them, sucked hard and brining his finger to Sam’s rim, rubbing it cautiously. Sam moaned loudly and he took that as a sign to continue, pushing in. Now this…Dean could do. He pumped his finger in and out, making Sam thrust back onto his hand, Sam always did like bottoming. Dean must have picked up on that because he pulled his finger out and pulled off Sam’s cock, spinning him around and pushing his lower back to down so that his ass was in front of his face. He sucked two fingers into his mouth and rubbed at Sam's rim again, “Oh yes, Dean, that’s good, I can take it”

Dean leaned in and kissed Sam's cheek, biting into the flesh as he pushed his fingers in, pumping slowly before Sam rocked back, making him move faster, scissoring his fingers against his prostate, “Like that?” he groaned, watching Sam take his fingers, biting at his flesh again.

“Oh fuck yes, Dean…Want it, oh yeah, just like that…Ahh fuck!” the younger boy grunted.

Dean already started getting hard again while he blew Sam, and he said in a low voice, “Think you could take my cock?”

Now this…this made Sam moan, “Yes, oh god, please fuck me, Dean”

Dean pulled his fingers out, “Bed, now”

He smacked Sam's ass and got up, picking up his clothes and Sam’s and followed Sam to the bed. When Sam got in, Dean slammed the door shut and pushed him onto the bed, his mouth immediately crashing into the younger boys, rough yet soft. The feeling of their cocks pressing together had the both of them moaning into each others mouths as they rutted together. Dean’s muscles rippled as Sam's hands slid down his back, and palmed his ass, “Fuck…Dean come on…want it” Sam groaned. 

“Mm..yeah, okay I got you Sammy” Dean grunted, sitting up and pushing his legs apart, his hand trailing back to Sam's rim, “One sec” he said, getting off the bed and digging in his night stand. He pulled out a bottle of lube and a condom, sliding it on after giving himself a few pumps, then slicked up his cock and and pressed his tip against Sam's rim, “You sure?” he asked quietly.

Sam nodded and slid his hands up Dean’s arms, “Hell yeah”

Dean smiled and began pressing in, “Holy fuck…So fucking tight baby…oh-shit!” He had never felt anything like this before. The tight heat felt amazing around him and he watched as Sam took every inch with little resistance, “Oh yeah…fuck that’s hot” he grunted.

“Oh, Dean…fucking….so big” Sam panted as he stretched him. After adjusting, Sam rolled his hips and moaned, trying to get him to move. “Come on Dean…want it”

Dean bit his lip and started moving his hips, “Ahh fuck” he grunted as he began to pump in and out of Sam, feeling his hard cock pressed against Dean’s stomach as he leaned down to kiss Sam, “So tight baby”

Sam moaned into his mouth, his tongue dominating Dean’s as he focused on not coming so soon. “You feel amazing Dean…who fucking knew” Sam chuckled lightly but it turned into a loud moan as the blonde hit his prostate, “Fuck!”

“That it? I find it?” he panted against Sam's lips. He smiled when Sam nodded, the younger boy's hands digging into his biceps, “So fucking hot like this…Didn’t know it would feel so good Sam…God fucking- oh yeah”

Sam clenched around him, “H-harder” Dean sat up, his hands at Sam's waist so he could hold Sam while he pounded into him with everything he had. He then took Sam's cock in his hand and used Sam's pre-cum to pump him simultaneously with his thrusts. “Oh god! G-Gonna come Dean!”

“Ahh!” he yelled, thrusting harder, “Come on, cum for me Sammy…Wanna see you c-come”

With the combined sensation of his fisting his cock, pounding into his prostate, and that deep voice commanding him, Sam came hard, shuddering and yelling his name. Dean threw his head back, panting as he finally let go, his hips faltering, now slowly working the both of them through the amazing orgasms they both experienced. 

They were both breathing hard as he pulled out, wincing. He got up to dump the condom into the trash can and came back to bed, flopping down next to Sam and resting his hand over his stomach, “Holy shit” 

“Yeah…that was…”

“Amazing” he finished with a gruff laugh, “I never…fuck…that was great”

Sam smiled and looked over at him, his face red and sweaty, “So…you’re okay with it?”

Dean turned to Sam, “Hell yeah…We are so doing that again”

“Good” Sam said, and kissed him.

Dean kissed Sam back and let his hand trail down his arm 

Sam smiled, “Yeah…are you okay with…us?”

“Oh yeah, more than okay” he said, “So completely okay” he kissed the younger boy again, swiping his tongue across Sam's bottom lip and leaning up to deepen it. Sam's eye brows shot up in surprise when he groaned.

Sam pulled away, “Easy there tiger…I need a little recovery…you really did a number on me”

He smirked and pecked Sam's lips, moving to kiss across his jaw, nibbling at Sam's ear lobe, “Maybe I want you to do a number on me” he whispered huskily into Sam's ear.

A shiver went down Sam's spine, “Oh yeah…I can do that” he replied, rolling Dean over and kissing him hard. Sam couldn’t help but smile into the kiss and he couldn’t wait until he got to be top for once. 


End file.
